Lithium hydroxide, monohydrate → (+/-)-(E)-2-(7-bromo-1'-(3-(2-(trifluoromethyl)phenyl)acryloyl)-2,3-dihydrospiro[indene-1,4'-piperidine]-3-yl)acetic acid

HRID 390145Notes

Reaction equation

HRID 390145 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:29]=1[C:9]1([CH2:14][CH2:13][N:12]([C:15](=[O:28])/[CH:16]=[CH:17]/[C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[C:24]([F:27])([F:26])[F:25])[CH2:11][CH2:10]1)[CH2:8][CH:7]2[CH2:30][C:31]([O:33]CC)=[O:32].O[Li].O>C1COCC1.CO.O>[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:29]=1[C:9]1([CH2:10][CH2:11][N:12]([C:15](=[O:28])/[CH:16]=[CH:17]/[C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[C:24]([F:25])([F:27])[F:26])[CH2:13][CH2:14]1)[CH2:8][CH:7]2[CH2:30][C:31]([OH:33])=[O:32]

Participants

6

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 44226472(+/-)-(E)-ethyl 2-(7-bromo-1'-(3-(2-(trifluoromethyl)phenyl)acryloyl)-2,3-dihydrospiro[indene-1,4'-piperidine]-3-yl)acetate

Product 1

HCID 58295679(+/-)-(E)-2-(7-bromo-1'-(3-(2-(trifluoromethyl)phenyl)acryloyl)-2,3-dihydrospiro[indene-1,4'-piperidine]-3-yl)acetic acidYield 48.6%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

(±)-(E)-ethyl 2-(7-bromo-1′-(3-(2-(trifluoromethyl)phenyl)acryloyl)-2,3-dihydrospiro[indene-1,4′-piperidine]-3-yl)acetate (13 mg, mmol) was dissolved in THF (0.4 mL) and MeOH (0.8 mL). A solution of LiOH.H2O (10 mg) in water (0.4 mL) was added. The mixture was stirred at rt for 5 d. The reaction mixture was submitted directly to preparative HPLC to afford (±)-(E)-2-(7-bromo-1′-(3-(2-(trifluoromethyl)phenyl)acryloyl)-2,3-dihydrospiro[indene-1,4′-piperidine]-3-yl)acetic acid (6 mg, %) as a solid. LC-MS Method 1 tR=1.92, min, m/z=522, 524.

Sources & evidence

ORD record
ord-48ac65f1e3dd47f48cf3aa69561990e3
Source dataset
uspto-grants-2013_02
Patent number
US08383629B2

Reaction notes

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